Jonas's desperate attempt to bring his son back to life, only to find out that he can't.

Caroline finally confessing to Matt that she is a vampire... only for him to react with horror and loathing, before simply emotionally collapsing.Particularly shattering and awful in a show where characters confessing their supernatural nature had been received with heartwarming degrees of acceptance.

Elena breaking down and confessing to Stefan that she doesn't want to be a vampire.

Jenna and John's deaths, especially John's letter to Elena read over the funeral montage. Even if you hated the guy, he sacrificed himself for his daughter.

Damon telling Stefan that he's been bitten by a werewolf. Stefan's expression is as heartbreaking as Damon's resignation.

In the season finale: Damon dying. Even though we knew he would survive in the end, it was still tragic to hear him tell Elena he loved her and to apologize to Stefan - who, meanwhile was out sacrificing himself to Klaus to save his brother.

In the season 3 opener "The Birthday", the phone call between Stefan and Elena made even die-hard Delena fans tear up.

In "The Birthday", when Elena gets up and throws the curtains open, seeing how she has to steel herself before doing that and the fact that it's almost certainly been that way every morning since Stefan disappeared is heartbreaking.

Klaus compelling Stefan to switch off his humanity while Elena watches in horror. At first Stefan fights the compulsion of an Original, but inevitably, it works.

Anna finding her mum again in "Ghost World.

The Original family's story itself is a Tearjerker, especially considering the fact that Mikael and Esther only turned their children so they could protect them from the werewolves, after their youngest son's tragic death. And then they all die and scatter.

The end of "Ordinary People", with Rebekah breaking down sobbing after learning that Klaus killed her mother.

YMMV but something about Elena telling Damon they have to let Stefan go is heart wrenching.

Caroline having to slowly watch her father die when he refuses to drink blood to complete the transition.

Damon's attempted Suicide By Sunlight, especially when one remembers his asking Elena to forgive him, her refusing, and his telling her to take all the time she needs - all the time knowing that he will die soon and keeping it from Elena.

She migth be have been a False Friend and The Vamp to Damon, but seeing Sage sobbing histerically over Finn's death, especially sense they where So Happy Together minutes before and where a true example of Eternal Love is acutally rather painful

When Alaric refuses to complete the transition, and everyone comes to say goodbye to him. Subverted later when a possessed Bonnie feeds him her blood, turning him into a vampire hunter

Let's be honest, this particular scene had several tearjerkers all put together. First there was Alaric saying goodbye to Elena and Jeremy, and telling them being their guardian was the closest he came to the life he wanted. Then the above-mentioned gathering of pretty much the entire cast. And finally, when Damon goes into the tomb to share one last drink with Alaric, and briefly hesitates to cap the bottle.

Rebekah breaking down when Alaric stakes Klaus right in front of her.

Damon's goodbye to Elena as she and Matt drive back to Mystic Falls. Sobbing, she tells him that she's never fallen out of love with Stefan and that maybe if they'd met first... And Damon actually did meet Elena first on the night her parents died. And he compelled her to forget about it.

Seeing Elena's final moments with her dad during the car crash and the parallels to it when she sacrifices herself so Stefan can save Matt, like her dad did with Stefan.

Caroline and Tyler's tearful goodbye after they find out about Klaus' death. And Tyler making Caroline promise to tell his mother that he got out of town like he said he would.

Possibly subverted, since it remains to be established whether that was really Klaus possessing Tyler rather than Tyler himself.

Damon cradling Alaric as he dies. His stricken mantra of 'You can't be dead, you can't be dead,' and you know he's thinking about Elena

Though he's probably thinking about his only friend as well. In that moment he thinks he's lost them both.

When the ghost of Alaric - the real Alaric - comes to say goodbye to Jeremy, and the look on Jeremy's face as he realizes that Elena is dead as well

Basically most of The Departed is a magical tear-generating machine. The flashbacks are upsetting since we know where they're going; the various tearful goodbyes, the melancholy musings...

The Rebekah and Klaus scene in 4x01 .... Actually, Rebekah in 4x01 in general.

At the end of season 3/beginning of season 4, Elena becomes a vampire. All that struggling to hold on to her humanity, in stark contrast to a certain other vampire-dating girl, we might add, and it's all for nothing.

Even worse, because of her doppleganger nature, Elena can't feed on animals or from blood bags. Meaning Elena has no choice but to bite people, running the very real risk of killing someone.

The end of "Memorial", where the gang sends off lanterns in memory of everyone they've lost and the following scene of Damon talking to Alaric 's gravestone

And unbeknownst to him, Alaric's ghost is sitting right there, completely quiet throughout Damon's tirade about how he's left him to 'watch over the kids.' It's only when Damon leaves that Alaric speaks: "I miss you too, buddy."

Rebekah's speech to Klaus before he daggers her in The Five.

"Go right ahead. Laugh at the girl who loved too easily, but I would have rather lived my life than yours, Nik. No one will ever sat around a table telling stories about a man who couldn't love. Look me in the eyes and do it, coward. Do it!"

The entirety of "We All Go A Little Mad Sometimes". Whether it's Tyler and Hayley mourning their hybrid friends, Klaus saying that he was tormented by the hunter's ghosts for 52 years or Elena's hallucinations, including her mother telling her to kill herself, it causes much weeping.

Jeremy becoming one of the Five and getting the uncontrollable urge to kill every vampire around him. Including his own sister.

Elena's reaction to the news, especially when she's told that he's killing vampires so that they can find the cure for her vampirisim: "If regaining my humanity means that Jeremy loses his, then I don't want this anymore."

Damon finding out that in order to break his sire bond with Elena, he has let her go and live her own life. Even Stefan - the person who stands the most to lose over this - feels sorry for him and what he has to do.

And in the same episode, Damon thinks about revoking the sire bond with Elena. She begs him not to. Then , in the next episode, he orders her to go home while he makes sure that Jeremy's mark grows without revoking the sire bond Even worse is that at the same time that's happening, Stefan finds out that Damon lied to him about doing so earlier that day, and Caroline more or less tells him that he and Elena have slept together. His reaction is heartbreaking.

Tyler's emotional breakdown about his mother's death.

Elena being compelled by Rebekah to confess her true feelings for the Salvatore brothers. She admits that she's in love with Damon - sire bond or no - , and that while she loves Stefan, she's not in love with him anymore, because he sees her vampiric existence as a mistake to be fixed.

And Stefan's reaction to this? To ask Rebekah to erase every memory he has of Elena. Because forgetting entirely is preferable to dealing with his heartbreak.

Rebekah confessing that she wants the cure so that she can have a normal life: to live, and dance, have children and grow old with someone who loves her. What makes this scene even worse is that she's confessing this to Stefan, who'd spent the entire evening with her at the cancelled school dance, just so he can get her dagger to put Kol down. And she just gives him the dagger, fully expecting him to use it on her, just like everyone else has done in her life. That's how badly she's been let down/betrayed/manipulated by people throughout her vampiric existence. Which makes Stefan's decision not to use it a Crowning Momentof Heartwarming

Klaus' reaction when he sees Kol's body burning in the middle of the Gilbert house. They had their differences and were dysfunctional at best, but the sheer loss and fury on his face when he realizes that Jeremy and Elena killed his little brother.

Rebekah's reaction is just as bad. Never mind that Kol had just tried to kill her using that stake...

The saddest thing about this is Kol's last conversation with Rebekah and Klaus. Rebekah, he tried to kill in his insane determination not to have Silas raised. Klaus, he called up and accused of plotting his death when he was in Elena's house. And Elijah? He's so filled with disgust with the rest of his siblings that he hasn't even been seen since season three. Kol died, not knowing that Klaus was rushing over to save him, and that his brother and sister did love him despite everything they've done to each other.

Then Fridge Horror sets in when you realize that Kol's charred remains are what's keeping him company for the three to four days that Klaus is sealed in the Gilbert home....

He might be a Manipulative Bastard, but it's hard not to feel for Atticus Shane in the flashback when he sees his dead wife again. It's clear that he's doing what he's doing just to have his family back again, and the look on his face when she reaches out and touches his face...and then the next episode makes it worse when it's revealed Caitlin's 'ghost' is just Silas' hallucination, used to control Shane into bringing about his return.

How about Bonnie after she sees what she thinks is the ghost of her Grams? And after Jeremy figures out that it's just a hallucination caused by Silas to control her, the spirit disappears, and Bonnie just looks around with tears gleaming in her eyes.

Tyler and Caroline's emotional goodbye after Klaus "mercifully" agrees to give Tyler a headstart before he starts hunting him down. Caroline tearfully tells Tyler that she can't say goodbye to him again, and Tyler says "This isn't goodbye. It's until we find a way..."

The entirety of "Stand By Me"

To elaborate: Jeremy is killed, permanently this time. His ring won't bring him back again, since as a Hunter he counted as a supernatural creature. Elena is in denial for the whole episode, waiting and waiting for the one hope she has, that Bonnie will find a way to bring him back. And when that fails, Elena snaps as it dawns on her that her little brother - the only family she has left in the world - is gone for good. She asks Damon to take his body downstairs, so that she can douse it - and the whole house - in lighter fuel so she can burn everything down.

Elena: What else are we supposed to do with the body, Caroline?! I-I mean (blinks back tears), there's no room in the Gilbert family PLOT! (throws pictures to the ground, they shatter) Jenna and John took the last spots! (lights the match)

Stefan: No, no...Elena, stop...

Elena: There's nothing here for me anymore, Stefan! Every inch of this house is filled with memories of the people that I love that have died. (sobbing) My mom, my dad, Jeremy, and Jenna, and Alaric...John, even John! I mean, they're all dead! Everyone is dead! (matchstick burns perilously low, she ignores it) S-So how am I supposed to...I-I can't, I can't even, th-there's nothing left for me-Aaah! (drops matchstick, Damon catches and extinguishes it)

Damon: Elena...I need you to calm down...

Elena: NO! No, I can't...(drops to her knees and wails) Ican'tIcan'tIcan't...I can't! (openly sobbing) No...it hurts, it hurts....just make it stop...please make it stop, it hurts...(continues to cry)

And then Damon makes her turn off her humanity before she has a complete breakdown. Yet, she still burns the house down anyway, because 'it's the best cover story' and she doesn't want to come to this house anymore. Her grief and sorrow is still that complete, even with her emotions gone.

Matt's reaction when he sees Jeremy's body. He tries to help Elena see through her denial, and has to be strong for everyone else. It's only when he's alone that he falls to pieces.

Not to mention, Caroline's constant calls to Tyler knowing that he won't answer her back. She seems to be less sane with each one.

Caroline's frantic attempts to resuscitate her mother in 4x21. It eventually works, but not after we see Caroline begging and sobbing and yelling that she's supposed to watch her graduate from high school....

Caroline full stop in this episode, thanks to Silas and his vicious Mind Rape..

It overlaps with Crowning Momentof Heartwarming, but seeing Elena's grief-stricken, shocked reaction when Damon snaps Matt's neck...and then her joy when she finds out that he was wearing Jeremy's ring...and then watching her sob and cry as the guilt and weight of all her actions finally bears down on her.

Rebekah, after being left all alone by her only two brothers. Just watching her trying to make up with the main cast, with no agenda whatsoever, so lonely and desperate for friends that she's making amends with the people who have no reason to even trust her at this point. And worse is that the only person who really tries to warm up to her is Matt.

And when Kol comes back in 4x22, Rebekah's shocked and happy expression gets wiped off her face when Kol makes it more than clear that he's only left the other side to drag Elena there himself, the whole situation ending with Kol throwing a broken bottle into Matt's arm before leaving. It's obvious that all Rebekah wants is to spend time with her brother, the only family she has left in Mystic Falls. And it's heavily implied that Kol is upset by how short his own family mourned him after he was killed, bitterly telling Rebekah that he has no need for her tears or her 'twenty-four hour grief.'

Elena kneeling in front of Jeremy's grave, sobbing and asking him how she's supposed to go on and let go of her grief. And then when Kol has her cornered, she just stares and tells him to kill her, that he'll be 'doing her a favour.'

Bonnie in 4x22, when she has to figure out a way to say goodbye to all her friends when the spell she uses to bring Jeremy back takes her life in exchange for his. So while the veil is still up, she goes through the motions of graduation.

The fact that she didn't even make it to her graduation alive.

And Caroline's happy, excited face when she talks about how the three of them are going to be roommates...

Bonnie's emotional goodbye to Jeremy, reassuring him that she'll be okay on the other side while he screams that she can't be dead.

Various times throughout the beginning of Season 4 where Damon is saving a seat at the Grill for Alaric even though he's dead

In the fifth season premiere, there is Bonnie's screams of horror and grief as Silas slits her father's throat right in front of the entire town square.

Hell, any scenes with Bonnie in general, keeping in mind that no-one aside from Jeremy knows she's dead. When the truth comes out, it's going to hurt Elena and Caroline.

It couldn't have happened to someone more deserving of the fate, but seeing Human!Katherine actually being vulnerable and visibly scared now that five centuries' worth of enemies will find out that she's no longer a vampire.

We learn that Stefan has been locked in that safe box for over three months and is in a constant state of waking up, drowning, dying and repeating that cycle indefinitely. He's suffering so much that he's begun to hallucinate conversations with Damon, who begs him to turn off his humanity so that - at the least - he won't care about being made to drown for eternity.

Katherine in 5.02. The resignation in her voice when she tells Matt and Jeremy that she understands - "I'm the leverage, I'm the object, I'm the thing everyone wants." As a human, all she was was the Doppleganger to Klaus, and as a vampire, she became the number one name on Klaus' shit-list and has been running ever since.

Matt's brief sojourn into the other side, when he finds Bonnie there and slowly realizes that she's dead. Even worse, once he jumps back into his body, he doesn't remember meeting her, and goes back to thinking that she's alive.

Bonnie in general in this episode. She's barely begun to make peace with her own death, and now she's grieving for her own father, who she can't even see because he was mortal and thus didn't end up on the other side.

When Elena hysterically tells Damon that she's been feeling Stefan all summer, that he's somehow reaching out to her and she knows he's in so much pain...right then and there, Damon agrees to help Elena find him. You can see the resigned hurt on his face as, once again, Elena's connection with his brother runs deeper than even his own love for her. But he'll still do the right thing and find him.

Damon's face when Qetsiyah tells him that the doppelgangers of Silas and Amara are always fates to find each other and fall in love. Effectively, even the universe is telling Damon that [[spoiler: he doesn't stand a chance with Elena. Subverted later when Damon basically tells destiny to screw itself.

The entire backstory of Qetsiyah. Silas seduced her so she could create the immortality spell. And then he abandoned her on their wedding night, and shared the elixir of immortality with Amara, his true love and Qetsiyah's own handmaiden. Like Silas, her psychosis is just a layer to hide how deeply betrayed and hurt she still feels.

Just before she sealed Silas away, Qetsiyah begged him to take the cure so they could live a human life together. Sure, she was torturing him with her powers at the time, but her expression showed how very much she just wanted him to be with her.

The last fifteen minutes of 5.04: Jeremy finally tells everyone the truth about Bonnie, and they hold a small memorial for her in the woods. Nobody can stop crying, and even Damon - who was irritated by Bonnie at best - can barely keep it together.

Bonnie relaying words of comfort to the group of friends through Jeremy.

Katherine in hysterics as she begs Damon not to let Silas drink all of her blood, telling him over and over that she doesn't want to die. It's made more heartbreaking in this context, because she's begging for her life so that she can have more time with Nadia, her biological daughter that she never even knew. Mitigated by the fact that even Silas drinking her blood doesn't kill her.

And from the same episode, Caroline begging Tyler to 'love me more than you hate Klaus!' They clearly love each other, but Tyler makes his choice and goes after Klaus, leaving Caroline a sobbing mess on the bed.

The precious few minutes that Silas and Amara spend together before she drinks his blood.

Hell, the effect of Amara's two thousand years in solitude and starvation. She is completely insane, hearing voices and she's in hysterics as she tells Silas that she 'can't live another day' before she drains him.

Gets even worse when she begs Silas to kill her. He doesn't want to lose her again, but they both know that their suffering has to end. Unfortunately, Stefan intervenes and kills Silas first. Meaning, all those millenia of waiting for his true love is wasted, and Silas ends up on the other side after all, while Amara passes on.

Katherine learns that the five hundred years she's spent as a vampire are now catching up with her, and she has at the most, a few months to live before she ages and dies. Nadia, completely unaware of what's going on with Katherine, begs her to come to Bulgaria with her so they can start afresh. Katherine coldly rejects her, says she wants nothing to do with her. It's clear from her expression that she doesn't want to hurt Nadia, but she feels it's the only way to keep her safe from the truth about what's going on with her.

Damon breaking up with Elena, out of his guilt and self-loathing about his dealings with the Whitmore family and Enzo and how those particular ghosts of his past put her in danger.

Katherine believing she is unworthy of love and sobbing hysterically because of it as she lies on her deathbed, and Stefan assuring her that she is. Mitigated by her selfish bid for life, but heartbreaking nonetheless.

Damon falling off the deep end after Elena (actually Katherine, who's body-surfed into Elena) breaks up with him.

Nadia's death and her final moments with her mother Katherine in 1.15.

Katherine's death itself, despite her antagonism over the years. The death of the prime facilitator of the entire series and that she is separated from Nadia for eternity is devastating.

Damon and Elena realizing how toxic they are to each other - but still unable to let go completely.

Enzo turns off his humanity rather than having to deal with the fact that Damon - the only friend he's ever had - murdered the woman he loved and whose memory kept him going for the seventy years he was held prisoner by the Augustines.

And then he commits suicide, by pushing off Stefan while he still has his hand wrapped around his heart. Stefan realizes what Enzo's death would do to Damon and has to lie about it, to keep his brother from going off the deep end.

Thanks to Markos escaping the Other Side, the supernatural purgatory is falling apart. Every single supernatural being there is being picked off one by one and vanishing into the same void that took Katharine: Vicki, Alaric, Grams...even Kol is terrified of what's going on when he meets Matt there. And the kicker? As the anchor to the Other Side, Bonnie's life is in danger as well. If it goes, she dies again. And like before, she can't bring herself to make peace with it or tell her loved ones about what's going on.

In 1.20, Bonnie says that if a ghost is emotional enough, they can interact with the world of the living. It kind of puts Enzo's actions into something even more tragic when you consider how much hate and fury he must have been feeling to be able to torment Damon and his loved ones so effortlessly.

In the Season 5 finale, Luke stops Liv's spell before it's finished, trapping Bonnie and Damon on the collapsing Other Side. The best Bonnie can do is tell Elena that Damon is present and give them a moment, leading to this epic, heartbreaking speech:

Damon: Even if I wanted to apologize, you couldnít hear me. So I wonít.

Damon: I donít have a choice, baby. You are by far the greatest thing to have ever happened to me in my 173 years on this earth. The fact that I get to die knowing that I was loved, not just by anyone, but by you? Elena Gilbert? Thatís the epitome of a fulfilled life. Itís never going to get any better than this. I peaked. I love you, Elena. Bye.

Followed by Bonnie and Damon standing together and holding hands as they wink out of existence.

Bonnie: Do you think it'll hurt?

Damon: I don't kn-

The fact that every supernatural character who died on the show and never made it back from the Other Side is gone for good, which - unless there's a way out - means that Vicki, Grams and Lexi are never coming back.

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